CO-Boosted Protocol for the Photocatalytic C−H Thiolation of Aldehydes Using Phenylthiobenzenesulfonate

Lin Wei Pan; Nobukazu Taniguchi; Mamoru Hyodo; Ilhyong Ryu

doi:10.1002/ejoc.202400138

CO-Boosted Protocol for the Photocatalytic C−H Thiolation of Aldehydes Using Phenylthiobenzenesulfonate

Lin Wei Pan, Nobukazu Taniguchi^*, Mamoru Hyodo, Ilhyong Ryu^*

^*此作品的通信作者

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1 引文斯高帕斯（Scopus）

摘要

The formyl C−H thiolation of aldehydes using thiosulfonates and the decatungstate anion as a photocatalyst is reported. Using this photocatalytic protocol together with a CO atmosphere, both aromatic and aliphatic thioesters can be synthesized in good yields. The transformation consists of a cascade of double S_H2 reactions, HAT and an ArS group transfer. CO atmosphere effectively limits the extent of decarbonylation of acyl radicals that are generated in the reaction.

原文	English
文章編號	e202400138
期刊	European Journal of Organic Chemistry
卷	27
發行號	28
DOIs	https://doi.org/10.1002/ejoc.202400138
出版狀態	Published - 22 7月 2024

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title = "CO-Boosted Protocol for the Photocatalytic C−H Thiolation of Aldehydes Using Phenylthiobenzenesulfonate",

abstract = "The formyl C−H thiolation of aldehydes using thiosulfonates and the decatungstate anion as a photocatalyst is reported. Using this photocatalytic protocol together with a CO atmosphere, both aromatic and aliphatic thioesters can be synthesized in good yields. The transformation consists of a cascade of double SH2 reactions, HAT and an ArS group transfer. CO atmosphere effectively limits the extent of decarbonylation of acyl radicals that are generated in the reaction.",

keywords = "S2 reaction, acyl radical, carbon monoxide, thioester, thiosulfonate",

author = "Pan, {Lin Wei} and Nobukazu Taniguchi and Mamoru Hyodo and Ilhyong Ryu",

note = "Publisher Copyright: {\textcopyright} 2024 Wiley-VCH GmbH.",

year = "2024",

month = jul,

day = "22",

doi = "10.1002/ejoc.202400138",

language = "English",

volume = "27",

journal = "European Journal of Organic Chemistry",

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TY - JOUR

T1 - CO-Boosted Protocol for the Photocatalytic C−H Thiolation of Aldehydes Using Phenylthiobenzenesulfonate

AU - Pan, Lin Wei

AU - Taniguchi, Nobukazu

AU - Hyodo, Mamoru

AU - Ryu, Ilhyong

PY - 2024/7/22

Y1 - 2024/7/22

N2 - The formyl C−H thiolation of aldehydes using thiosulfonates and the decatungstate anion as a photocatalyst is reported. Using this photocatalytic protocol together with a CO atmosphere, both aromatic and aliphatic thioesters can be synthesized in good yields. The transformation consists of a cascade of double SH2 reactions, HAT and an ArS group transfer. CO atmosphere effectively limits the extent of decarbonylation of acyl radicals that are generated in the reaction.

AB - The formyl C−H thiolation of aldehydes using thiosulfonates and the decatungstate anion as a photocatalyst is reported. Using this photocatalytic protocol together with a CO atmosphere, both aromatic and aliphatic thioesters can be synthesized in good yields. The transformation consists of a cascade of double SH2 reactions, HAT and an ArS group transfer. CO atmosphere effectively limits the extent of decarbonylation of acyl radicals that are generated in the reaction.

KW - S2 reaction

KW - acyl radical

KW - carbon monoxide

KW - thioester

KW - thiosulfonate

UR - http://www.scopus.com/inward/record.url?scp=85198108731&partnerID=8YFLogxK

U2 - 10.1002/ejoc.202400138

DO - 10.1002/ejoc.202400138

M3 - Article

AN - SCOPUS:85198108731

SN - 1434-193X

VL - 27

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 28

M1 - e202400138

ER -

CO-Boosted Protocol for the Photocatalytic C−H Thiolation of Aldehydes Using Phenylthiobenzenesulfonate

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